Gregg Starr spent the last few months of his career becoming, in the words of his own plastic surgeon, a “supernatural” specimen. Now he is facing allegations that the money behind that transformation, and much more, came from a grieving widow who says she was manipulated out of nearly $6 million.
Marianne Flippo, 49, filed a lawsuit against Starr, 38, in Manhattan Supreme Court on September 14, accusing the former West Point cadet turned high-end entertainer of exploiting her while she was mourning her husband and recovering from surgery.
According to sources, Flippo is asking the court to order the return of $5.95 million, cover her legal costs, and block Starr from spending whatever remains of the money she says he took.
The case traces back to the death of Flippo’s husband, Chad Flippo, who joined Roblox during its early startup days and held multiple patents tied to the company’s software. The two had been a couple since they were 13 years old and were married for 28 years before he passed away in August 2024. Court filings state he left behind substantial wealth, which passed to Marianne.
Grief sent her looking for treatment that had grown difficult to obtain in the United States, and she traveled to Italy to find it. Needing help navigating the country, she turned to an agency called Cowboys4Angels and paid roughly $27,000 to bring along a companion who spoke Italian: Starr.
According to the lawsuit, Flippo did not initially understand that the agency dealt in adult services, believing instead that she had hired a personal assistant. She says she and Starr kept separate hotel rooms on the trip, and it was only after the agency kept reaching out afterward, telling her that Starr missed her, that a relationship began to form.
By March 2025, Flippo had allegedly paid about $150,000 to secure six months of Starr’s exclusive companionship. He eventually moved into her apartment on the Upper West Side, and the arrangement kept growing. Additional agreements pushed her total spending on his companionship to around $635,000, according to the filing.
It was around this stage, the lawsuit claims, that Starr told Flippo he wanted out of Cowboys4Angels for good, but that leaving would require her to buy out his contracts for $10 million.
Flippo says that request landed while she was in a vulnerable state, recovering from surgery, managing an infection, and taking prescription [ ] including gabapentin and codeine. She also lives with vascular Ehlers-Danlos syndrome, a rare condition that can heighten sensitivity to treatment.
Flippo’s affidavit describes a February 2026 lunch where Starr and an employee of the agency presented her with what was called an “Exit Agreement.” She claims she was pressured into signing it while confused and medicated.
“Unfortunately, I was not capable or perceptive enough to know these statements were false,” she wrote in the filing. “I now realize I was foolish.”
Her first attempt to wire the full $10 million was reportedly intercepted by JPMorgan Chase after the bank’s detection flagged the transfer. A second attempt through a different bank was also stopped.
Flippo alleges that Starr then had her open a joint account at Charles Schwab, a move that let him draw on the funds without setting off another review. She transferred $5.95 million into that account. Bank records cited by Fortune indicate Starr shifted $5,719,010.37 of it into an account solely under his control within weeks. By the end of June, the joint account held just $12.61.
Suspicion mounted when Starr allegedly began asking for another $4 million. During a July meeting, Flippo’s attorney, Larry Hutcher, pressed Starr on the arrangement, and the lawsuit claims Starr responded by threatening to keep the money already transferred unless she paid the rest.
The financial fallout reportedly extended into real estate as well. Flippo purchased a $15.9 million Manhattan mansion, believing it would become a shared home for her and Starr.
Starr has pushed back hard on the claims. Speaking to the Post, he said he was the one mistreated in the relationship and maintained that much of the money went toward joint expenses and charitable giving, adding that roughly $3 million of it remained untouched. His attorney told the Post that Starr’s version of events would come out “in due time.”
Behind the legal battle is a physical transformation that has drawn its own attention. Starr’s cosmetic overhaul was chronicled in detail on the social media accounts of Beverly Hills plastic surgeon Dr. Jason Emer, whose practice showcases uncensored footage of procedures under a “Patient Stories” banner.
Emer has framed Starr’s results as an example of what he calls the “Maxoris” ideal, a body- and face-sculpting standard built through cosmetic work. The changes reportedly touched Starr’s face, nose, chest and abdomen, and included liposuction, facial contouring and penile enhancement.
In one video, Starr laid out the plan bluntly: “So, we’re going to do a 360 lipo and then we’re doing a pen[]le injection, and we’re going to do some contour around the face.” Emer, sketching directly onto Starr’s chest, arms and glutes to map treatment zones, called the scope of the work “extensive” and described the intended outcome as “a 360, supernatural look.”
Starr later posted a video praising the results, saying Emer “was able to combine scientific precision with art and beauty,” and adding, “I just couldn’t be happier.”
An acquaintance who knew Starr told the Post they had heard the procedures amounted to nearly a full-body overhaul, saying, “I know it was basically full body.” The same acquaintance said Starr’s line of work was no secret among people who knew him: “Obviously, I knew the type of work he was involved with.”
Still, the allegations in Flippo’s lawsuit caught the person off guard. “He didn’t appear to be the type of person who would do that, but then again you never know,” they said.
Starr’s résumé stands in contrast to his current headlines. He graduated from the United States Military Academy at West Point in 2010 with a degree in chemical engineering, according to the academy’s alumni records and his LinkedIn profile, which also lists graduate coursework in biochemical engineering at Stanford and MBA and law studies at Northwestern.
He went on to work at the venture capital firm Panoramic Ventures before his time with Cowboys4Angels, an agency previously linked to Sean “Diddy” Combs, who reportedly recruited participants for his service. Starr has also modeled, appearing in photos from a New York Fashion Week show at Gotham Hall featuring SéSé KUTUR’s Vesper Kollection.
Roblox itself is not accused of any wrongdoing in the suit. Its only tie to the case runs through Chad Flippo’s early work at the company and the fortune it generated for the family he left behind.
